The Perks of Being a Podcaster Pt. 10

All of the following is complete and total fiction. Not a word of it occurred, nor would it.

The Perks of Being a Podcaster

by MrMaxLord

(MF, exhib, cons)

Chapter 10: Hailee Steinfeld

*****

Fresh off the end of my time in New York with Taylor and Ashley, I thought I was going to have a nice, easy going time on my train ride back to finish out my vacation. And I was mostly right. However, something told me the familiar face sitting across from me was going to keep things from being as calm.

"I have to admit," Hailee said, finding just the right spot for optimal comfort and, apparently, sexiness in her seat. "I didn't really expect to see anyone I know here. Not that I'm complaining, I just kind of chose a train specifically for that reason."

"Same here." I replied. "I mean, if I'm bothering you I could jump off the train."

"Awww, how sweet." she giggled. "Nah, I think I'll like the company. I love being on the show, but I've never really talked to you outside of it. This is the perfect chance to change that."

"I didn't know I was that interesting."

"Oh, don't be so coy," Hailee grinned. "Don't forget, we do kind of move in the same circles with some people. You've got a bit of a rep."

"A good one I hope."

"Well, it's one you have to live up to instead of living down."

"I hope it's not too lofty in that case."

"How about you join me for dinner and we can both find out? Besides, I'm actually kind of excited to eat on a train."

"I know, right? Weird."

"Then let's have a weirdo dinner together." We got up and walked together to the dining cart. The train was booked lightly, so getting a seat was a quick affair. As an added bonus, the dinner was going to be surprisingly private and cozy, as there weren't any people seated around us. In fact, the nearest occupied tables were on the other side of the car.

"I am really glad I made sure this was a lightly booked trip," I said, pulling out a seat for Hailee. "Not really a big fan of crowds. Which of course means I needed to take a vacation in New York."

"Ah yes, with that bastion of open space known as Manhattan," she said with a smile. "I hate crowds too, unless I'm in front of them. Like any person with a healthy ego that isn't desperately starved for attention."

"A typical entertainer in other words."

"Exactly." We both laughed, and weren't afraid to hide it, snorts and all. "I get it though. That's why I booked this train. I always like checking that stuff out. And this one got the prize."

"Why were you in New York? Vacation as well?"

"No, all business. No real fun stuff. Which is why, well, train. And it's just me. Not that I don't love my family and friends, I just really needed to decompress from everyone, including them. Too much work, too much personal stuff on my mind, and I thought, hey...trains. No paparazzi, and I can pretty much be alone with my thoughts whenever I want. I don't get that with airplanes. I mean, that's like pa central. And a cruise would have the same problem because there's no way I'm going out to sea without a bikini."

"Well, that's something to be thankful for."

"Hey, I know what I got, and I'm proud. And thanks for looking." Hailee gave me a wink, then sipped at her water. "Still, this seemed the best option, and I've never really traveled just for me, and definitely not on a train."

"Well, so far far as all that stress been eased?"

"Kind of. Work's the last thing on my mind."

"And the personal stuff? I asked.

"Look, I don't want to bore you with that," she said. "I mean, who wants to hear about some silly little drama?"

"Eh, why not? You tell me yours I'll tell you mine."

"Fair enough. Since I brought it up, I'll go first. Okay, so I've been seeing this guy, ya know? And I like him, a lot. I'm not seeing anyone else, neither is he...but we also never said that special thing to kind of signify we're a real thing."

"Of course, that romantic phrase "Don't fuck other people."

"Exactly," she laughed. "But, seriously, I don't even know if I want that. I mean, I'm not even twenty-one, do I want to be in a committed relationship. I mean yeah, I'm famous and that kind of makes casual dating a bit of a problem because how many guys ANY age want to deal with flashbulbs going off in their faces constantly? Like, if I break it off with this guy, what if I don't find another as good as him. On the other side...I'm young and want to have some fun. Some real fun. I don't want to be pushing forty and realize I had a boring ass life."

"I get it. Believe me, I do. I don't know if any of the supposed legends you heard about me involved the fact I almost got married when I was twenty-three."

"Really? What happened?"

"We broke up before I could propose. She met some other guy, and we ended it. We're still best friends, and in the long run honestly it kind of worked out pretty well in the fun department. Also add to the fact that if you have this much doubt you've pretty much already made your decision...I think you just want someone to point that out to you. If the thought enters your head this guy is holding your life back, then you already know it's over."

"Yeah, I guess you're right. He's just SO nice, I don't want to hurt him. But, I don't even know if I'm who I'm always going to be. I don't even know if I'm a close approximation of this future Hailee-type person."

"You might even become a cyborg."

"Oh yeah, totes." She gave me a smile, licking her lips as her eyes caught mine. "Now you. Spill it."

"My thing is I don't even know if I'm with the woman in question or not. It's like, one by one, every single wall in front of us is falling down except for her indecision on it. I mean, I can see she wants to, but she also doesn't want to go full blown commitment because of her work schedule. I mean, Maybe I should take that as a good sign, because it definitely comes across like she wants to make it, you know, official. She actually gave a deadline, when she's done shooting."

"Ah, so you got yourself involved with an actress," Hailee said. "Anyone I know?"

"I think I'll keep her like your guy pal, anonymous."

"Fair enough. So, with this girl, you really like her, she likes you, right?"

"Yeah."

"But you're not exclusive yet...has she had any boyfriends before?"

"Yeah." I replied. "Why?"

"Well, and this is purely based on my experience as an armchair therapist after watching Frasier on Netflix nonstop last time I had the flu, maybe she's nervous about it because she does more than like you, a lot more. She might not know how to deal with it and is, you know, kinda processing it right now. So, she wants some space and time to figure it out. Like...let me ask you a question, you've fucked other girls since she's said this, right?"

"Yeah. I mean, she made it pretty clear we weren't exclusive. And I don't mean that in a bad way."

"Oh course not," she assured. "I'm just saying, it's safe to say she's been having some fun as well. It's all about sorting it out. I'm sure once the dust has settled, things will be crystal clear. So, hang in there...but don't stop having fun."

"Oh, of course not. Though, not gonna lie, if I got a call from her tonight telling her to keep it in my pants, she's coming for me, then I'm doing it."

"Well, I certainly hope you don't get a call tonight." Hailee gave me wink. Before I could respond, our server arrived. We ordered our food, during which Hailee turned up the heat when I felt her massage my crotch with her foot while I ordered, grinning while biting down on her straw the whole time.

Despite this, the dinner was still very conversational. Hailee was a much better conversation in real life than she was as an interview, and she was a great interview. Somewhere along the dinner, the idea of checking out the trains observation car was brought up. Neither of us ever having heard of such a thing, it was an easy thing to agree on.

With dinner finished and server tipped, we headed to the deck. Like the dining car before it, the place was near abandoned. In fact, if not for us it'd be entirely empty. The walls and ceiling of the car were essentially one big window, and the room itself was oddly dimly lit, almost by candlelight.

"This has to be the supreme make-up spot for train enthusiasts," Hailee said. "The moon, the stars...fuck lighting."

"Is that a technical term?"

"Oh yeah, use it all the time on set. I remember being on the set of Romeo & Juliet and suggesting to the director that the fuck lighting wasn't fuck enough."

"You know, I do remember hearing Spielberg say something about fuck lighting on one of the Indiana Jones commentaries." She turned to me and smiled, the glow of the lighting making her brown eyes sparkle.

Hailee leaned her back against the glass of the window, arms folded, but friendly. "I don't know, I like the moonlight, but I kind of expected more to observe on the observation deck."

"Well, I hate to be the voice of dissent in our so far pleasant night of conversation, but I think my view is pretty good."

"Oooh, nice and cheesy," Hailee said, unfolding her arms. "I like it." I moved closer to her, face to face. My hands were on her hips now, Hailee actually holding them there with her own. "And initiative...very sexy."

"How sexy?"

"Very. And the only thing sexier I can think of is someone who knows when to cut the small talk and mmmmm!" her sentence was derailed by my kiss and her hands moved to wrap around my shoulders. Mine roamed her body, up and down and feeling every contour of her breasts, hips and ass.

My hand went under her skirt, feeling the dampness at her panties. I hesitated going forward until Hailee gave me the okay.

"Do it," she whispered. "We're alone...it's late...just do it..."

With that kind of argument, I'd be an idiot to say no. I pushed her underwear aside and slid my fingers into her wet hole. I felt her shiver a bit as I began to work on her, my pace building up briskly. We were alone, but that could change at any moment. That was half the fun...well, considering who I was about to fuck for me it would be more like one fourth of the fun, but still, same principle.

Hailee mewled and moaned, rolling her head back as I fingerbanged her, the sounds getting moist and sloshy. She was just on the edge, not a major orgasm, but a nice small one. But one look in her eyes and I knew that wasn't enough for her, and Hailee was more than ready to confirm that thought.

She moved forward, her hair just in front of those eyes. "Fuck me," she said, her open mouth in a smile. "Right here...let's have some fun..."

I answered her demand my spinning Hailee around and yanking her panties to her knees., Lusty laughs escaped her lips, soon replaced by moans of pleasure as I entered her from behind. Hailee braced herself against the large window of the observation car as I took her.

There was tenderness to be had. I nuzzled her neck and breathed in her scent, sweat mixed with Gucci Guilt. My hands roamed her body, going under her clothes instead of removing them, sandwiched between flesh and cloth.

I cupped her breasts, massaging them before teasing her nipples with my fingers. One hand moved down, over her toned stomach and down to her pussy. I reached under her skirt, grabbing her hand first to join with mine. Together, we worked her clit as I increased my pace into Hailee.

Soon she was pressed tightly against the glass as I drove into her, moaning in a high pitch desperate for more, and I gave her my all. If the lady wanted fun, who was I to deny it? And clearly, she was being successful in her quest...but we both wanted a bit more.

"Uh...ugh...Bart...uh...fuck...I..I want to fucking ride you...mmmm fuck...I want you to see my face while we fuck...fuck yes...ungg I want that..."

"You got it." I pulled out of her, still grasping her hand as I took a seat. She grinned wide, breathing deeply as she straddled me, then slowly sunk down on my cock. "Fuuuuuck, Hailee."

"Oh yes baby," She moaned. Hailee braced herself on the chair as began to build up her tempo. Nothing slow, but still a hint of sensuality. She knew every movement to make for the most pleasure, both visually and physically, tossing her hair in just the right way, the things she said with just her eyes.

My hands gripped her firm, round ass, kneading the toned muscle in my hand as Hailee continued her wild ride. She could barely contain her vocals, trying hard not to moan so loud the people in the next car might be able to hear...but at some point pleasure was going to outweigh the need for discretion. And with every thrust and grind, every moan we both let out grew louder and louder.

As we got closer and closer to our points of no return, Hailee leaned further and further back. Our pace increased more and more, Hailee nearly leaning all the way back, low moans escaping her mouth until finally, she felt the embers begin to ignite. She shot forward, pulling close to me. She grasped me by the face, and kissed me hard, moaning in my mouth as her orgasm hit her. She broke the kiss only to whisper-moan "Oh fuck!" as pleasure raced through her body. Seeing and feeling this all up close set me off as well.

"I'm gonna shoot Hailee," I growled. "Where..."

"In me," she said, choking on a breath. "Oh fuck, cum in me...cum in me Bart..." I held her tight and released in her, thrusting up once more as streams of my cum filled up the beautiful actress on top of me. When I was empty, Hailee softly pressed her lips to mine, the rested her head on my shoulder.

"Well," she said while catching her breath. "That was definitely fun."

"Definitely." I replied. "Not often you have the best train trip ever in the history of mankind on the first night."

"Bet we can top it on night number two," she giggled.